The present invention relates to the field of halogenated hydrocarbons and the manufacture and purification of same, and more particularly, but not exclusively, relates to processes for dehydrohalogenating tertiary halogenated hydrocarbons, which processes have utility, for example, in the removal of a tertiary halogenated hydrocarbon impurity from a manufacturing process stream.
1,3-Dichloro-1-propene is a useful commercial compound in the medical and agricultural fields. Dow AgroSciences, Inc., (Zionsville, Ind.) produces a mix of cis and trans isomers of 1,3-dichloro-1-propene under the trademark Telone II® for use as a soil fumigant to control nematodes.
1,3-Dichloro-1-propene is a by-product, or co-product, of the chemical reactions employed to produce allyl chloride, and thus commercial 1,3-dichloro-1-propene products can be made by isolating a byproduct fraction from an allyl chloride production plant that includes 1,3-dichloro-1-propene (referred to herein as a “Telone crude” fraction), and then subjecting the Telone crude to a distillation process to separate and recover 1,3-dichloro-1-propene from the other by-products and impurities that are produced in the allyl chloride manufacturing process and that separate into the Telone crude fraction. While distillation processing is suitable to achieve desired purity levels with respect to many of the by-products and impurities in the Telone crude, one particular tertiary chlorinated alkane species, 2-chloro-2-methylpentane, cannot effectively be separated from 1,3-dichloro-1-propene by distillation to meet desired purity levels.
There exists a need for processes effective to remove a 2-chloro-2-methylpentane impurity from 1,3-dichloro-1-propene and, more generally, a need to remove tertiary halogenated hydrocarbon impurities from a hydrocarbon product. The present application addresses these needs and provides additional benefits.